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Cheap flights from Boston (BOS) to Chicago (CHI)

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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Cheap flights from Boston to Chicago in March , April 2026

10 Mar - 08 Apr $ 152.00
BOS
Boston
Spirit Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Spirit Airlines
1 STOPS
BOS
Boston
Pick dates
28 Mar - 03 Apr $ 176.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
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12 Mar - 08 Apr $ 5,382.00
BOS
Boston
Spirit Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Spirit Airlines
1 STOPS
BOS
Boston
Pick dates

Last minute flights from Boston to Chicago

27 Mar - 31 Mar $ 205.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
Pick dates
10 Mar - 31 Mar $ 205.00
BOS
Boston
Spirit Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Spirit Airlines
1 STOPS
BOS
Boston
Pick dates
12 Mar - 31 Mar $ 10,561.00
BOS
Boston
Hawaiian Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
DIRECT
BOS
Boston
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One-way flights to Chicago from Boston

10:17 AM - 10:17 AM
United Airlines
0 Stops
2h 59m
BOS - CHI
$ 69
Kiwi
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6:00 AM - 6:00 AM
United Airlines
0 Stops
3h
BOS - CHI
$ 73
Kiwi
Pick dates
6:23 PM - 6:23 PM
United Airlines
0 Stops
2h 59m
BOS - CHI
$ 199
Kiwi
Pick dates

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

Related info for your journey
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.